Juncatrin B

Phenanthrenes from Juncus articulatus with Antibacterial and Biofilm Formation Inhibitory Activity.[Pubmed:39121346]

J Nat Prod. 2024 Aug 23;87(8):2068-2080.

Continuing our search for bioactive compounds in species from the Juncaceae family, Juncus articulatus was investigated. Ten previously undescribed phenanthrenes horizontal line articulins A-J (1-10) horizontal line and ten known compounds horizontal line juncuenin B, dehydrojuncuenin B, Juncatrin B, ensifolins E, F, H, I, K, juncuenin D, and luzulin A (11-20) horizontal line along with other compounds, have been isolated and identified. The isolated compounds were evaluated for antibacterial activity against Escherichia coli, Pseudomonas aeruginosa, methicillin-susceptible Staphylococcus aureus (MSSA), and methicillin-resistant Staphylococcus aureus (MRSA). Compounds 12 and 14 exhibited the most potent activity against planktonic and sessile MSSA and MRSA with minimum inhibitory concentration (MIC) values of 15.1 muM (12 for both bacterial strains) and 15.3 muM (14 for both bacterial strains). Compounds 15, 17, and 18 also exhibited activity against both strains, although to a lower extent, with MIC values ranging from 30.0 to 56.8 muM. The inhibition of biofilm formation of these compounds was observed at 15.1-114.3 muM. This study elucidates the phenanthrene composition of J. articulatus and the antibacterial effect of these compounds.

Unique Phenanthrenes from Juncus ensifolius and Their Antiproliferative and Synergistic Effects with the Conventional Anticancer Agent Doxorubicin against Human Cancer Cell Lines.[Pubmed:35335985]

Pharmaceutics. 2022 Mar 10;14(3):608.

Phenanthrenes are the main special metabolites of Juncaceae species from phytochemical, pharmacological, and chemotaxonomical points of view. The present study focused on the isolation, structure determination, and pharmacological investigation of phenanthrenes from Juncus ensifolius. Nineteen compounds, including 17 phenanthrenes, were identified from the methanol extract of the plant. Thirteen compounds, namely, ensifolins A-M (1-13), were obtained for the first time from natural sources. Four phenanthrenes [2-hydroxy-1,7-dimethyl-5-vinyl-9,10-dihydrophenanthrene (14), juncuenin B (15), Juncatrin B (16), and sylvaticin A (17)], 4-hydroxybenzaldehyde (18) and luteolin (19) were isolated for the first time from J. ensifolius. Ensifolins A (1) and B (2) are structurally unique phenanthrenes, considering that they are flavonoid- (1) or benzaldehyde-adducts (2). The antiproliferative activity of all isolated compounds against HeLa, COLO 205, and COLO 320 cancer cells and a non-tumor (MRC-5) cell line was tested using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl-2H-tetrazolium bromide (MTT) viability assay. The luteolin-substituted phenanthrene ensifolin A (1) proved to be the most active against all three cancer cell lines (IC50 values 3.9-12.7 muM) and showed good selectivity (SI = 4.95) in the case of COLO 205. The best selectivity was recorded for ensifolins D (4, SI > 5.15, HeLa), H (8, SI > 8.13, HeLa), and 17 (SI > 9.43, HeLa). The synergistic activity of the compounds with doxorubicin was also tested on HeLa cells, and ensifolins E (5) and H (8) exhibited very strong synergism (CI < 0.1). In conclusion, these phenanthrenes are worthy of further investigation.

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